Combinatorial Chemistry for Ligand Development in Catalysis: Synthesis and Catalysis Screening of Peptidosulfonamide Tweezers on the Solid Phase
2000; American Chemical Society; Volume: 65; Issue: 6 Linguagem: Inglês
10.1021/jo991628z
ISSN1520-6904
AutoresArwin J. Brouwer, H.J. van der Linden, Rob M. J. Liskamp,
Tópico(s)Asymmetric Hydrogenation and Catalysis
ResumoOn the basis of a pyrrolidine tweezer 1, a library of peptidosulfonamide tweezers (15a-e, 16a-e) was synthesized on the solid phase. This library was screened in a simultaneous substrate screening procedure for the ability to enantioselectively catalyze the Ti(O-i-Pr)(4)-mediated addition of diethylzinc to aldehydes. One of the best solid-phase tweezer catalyst (i.e., 16d, giving an ee of 32% in solid-phase catalysis) was resynthesized in solution (compounds 20 and 21). The now homogeneous solution-phase catalysis showed even better enantioselectivity (i.e., up to 66%).
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